I’ve been delighted but surprised to find some University of Chicago homies in the tech business recently — because tech entrepreneurship seems totally inimical to the values for which Chicago has always stood: devotion to the past, reliance upon primary sources or direct experimental data, the Socratic method, the ability to write reams of crisp expository prose on command, genteel leather elbows on a tweed coat academicism, political extremism (thankfully totally theoretical), and a general lack of contact with reality. I’d like to be able to say that an intense liberal-arts education prepares you for all things blah blah… but honestly, I would have to admit that the form practiced at Chicago prepares you for many things unrelated to getting a job in a competitive industry, working effectively in teams, or managing your fellow human beings.

For years the only other practicing techie alum I knew (besides my own Timboy, of course) was John Wiseman, who proved his great intelligence by starting grad school with Tim but then dropping out way earlier. Then at OSCON 2004 I met Ryo Chijiiwa, whose extensive Open Source social software experience eventually led to him joining the Yahoo 360 team. I’ve heard he’s already recruited another recent grad, Yitz, to join him there; and we’ve talked about non-time-consuming things we might be able to do to help alumni who might want to make the trek out here.

Then in the process of meeting venture capitalists recently, I was re-introduced to Lara Druyan of Allegis Capital — who was in the same freshman dorm as me! I actually know of two other Silicon Valley VCs from Chicago: Joi Ito of SixApart (I guess he’s an ex-VC now, and bizarrely enough I’ve never met him in person), and Tae Hea Nahm of Storm Ventures (although he’s Law School, so I dunno if he counts :-)).

Lara introduced me to Mark Goodstein, founder of the desktop search company X1 — we had lunch recently and a good laugh about some crazy Alpha Delts we had known. And at OSCON 2005 we met Alex Bosworth of Seattle software startup Sourcelabs, who runs the Open Source wiki called Swik. He dropped out of Chicago, so he lacks the full bitterness of the true University of Chicago grad; but I think I can still include him in this blog post.

Any other U of C alumni out there in the tech biz? Maybe we could scrape enough bodies together for a drinks night or something.